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DOI: 10.1055/sos-SD-027-00002

Aggarwal, V.; Richardson, J.Science of Synthesis, (20042762.

One of the most commonly employed methods for the generation of sulfonium ylides is by deprotonation of sulfonium salts under solidliquid phase-transfer conditions; typically combinations of organic solvent and solid base are employed. This method is most commonly employed for the generation of nonisolable ylides, which are further reacted in the same flask. For example, potassium hydroxide in acetonitrile/water is used to generate benzylidenesulfonium ylides 103 in a highly efficient manner at room temperature,[‌193‌,‌195‌] and the stable sulfonium ylide 104 is obtained in 95% yield using a mixture of saturated aqueous potassium carbonate and saturated aqueous sodium hydroxide and chloroform (Scheme 55).[‌196‌] This method for ylide generation is less rapid than other methods, but such disadvantages are offset by its convenience and efficiency.

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